CN107849254B - Polyorganosiloxane and copolycarbonate prepared using the same - Google Patents
Polyorganosiloxane and copolycarbonate prepared using the same Download PDFInfo
- Publication number
- CN107849254B CN107849254B CN201680043792.8A CN201680043792A CN107849254B CN 107849254 B CN107849254 B CN 107849254B CN 201680043792 A CN201680043792 A CN 201680043792A CN 107849254 B CN107849254 B CN 107849254B
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- hydrogen
- polyorganosiloxane
- alkylene
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- 239000000126 substance Substances 0.000 claims description 46
- -1 phenyl Chemical group 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 230000000704 physical effect Effects 0.000 abstract description 7
- 229920005668 polycarbonate resin Polymers 0.000 abstract description 4
- 239000004431 polycarbonate resin Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 3
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 3
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000000774 hypoallergenic effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GPFJHNSSBHPYJK-UHFFFAOYSA-N (3-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1 GPFJHNSSBHPYJK-UHFFFAOYSA-N 0.000 description 1
- JAKQQNJMLCVDDC-UHFFFAOYSA-N 1,1'-biphenyl;carbonic acid Chemical compound OC(O)=O.C1=CC=CC=C1C1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 JAKQQNJMLCVDDC-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- HREXIBFZDJHFCF-UHFFFAOYSA-N 2,6-dibromo-4-propylphenol Chemical compound CCCC1=CC(Br)=C(O)C(Br)=C1 HREXIBFZDJHFCF-UHFFFAOYSA-N 0.000 description 1
- HNDVYGDZLSXOAX-UHFFFAOYSA-N 2,6-dichloro-4-propylphenol Chemical compound CCCC1=CC(Cl)=C(O)C(Cl)=C1 HNDVYGDZLSXOAX-UHFFFAOYSA-N 0.000 description 1
- HJZJMARGPNJHHG-UHFFFAOYSA-N 2,6-dimethyl-4-propylphenol Chemical compound CCCC1=CC(C)=C(O)C(C)=C1 HJZJMARGPNJHHG-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- UFUBQDNODUUQTD-UHFFFAOYSA-N 2-bromo-4-propylphenol Chemical compound CCCC1=CC=C(O)C(Br)=C1 UFUBQDNODUUQTD-UHFFFAOYSA-N 0.000 description 1
- WRLVTKZXVVEUPL-UHFFFAOYSA-N 2-chloro-4-propylphenol Chemical compound CCCC1=CC=C(O)C(Cl)=C1 WRLVTKZXVVEUPL-UHFFFAOYSA-N 0.000 description 1
- FDIPWBUDOCPIMH-UHFFFAOYSA-N 2-decylphenol Chemical compound CCCCCCCCCCC1=CC=CC=C1O FDIPWBUDOCPIMH-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- QEMHBAGGYKJNSS-UHFFFAOYSA-N 2-icosylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O QEMHBAGGYKJNSS-UHFFFAOYSA-N 0.000 description 1
- WCRKLZYTQVZTMM-UHFFFAOYSA-N 2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=CC=C1O WCRKLZYTQVZTMM-UHFFFAOYSA-N 0.000 description 1
- JOONSONEBWTBLT-UHFFFAOYSA-N 2-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1O JOONSONEBWTBLT-UHFFFAOYSA-N 0.000 description 1
- OREKREJVUNVFJP-UHFFFAOYSA-N 2-triacontylphenol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1O OREKREJVUNVFJP-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/085—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/18—Block or graft polymers
- C08G64/186—Block or graft polymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
- C08G77/448—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences containing polycarbonate sequences
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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Abstract
The present invention provides a novel polyorganosiloxane capable of preparing a copolycarbonate having improved weather resistance and fluidity while maintaining inherent physical properties of a polycarbonate resin, and a copolycarbonate prepared using the polyorganosiloxane.
Description
Technical Field
Cross Reference to Related Applications
This application claims the benefit of korean patent application No.10-2015-0125677, filed on 4.9.2015, the disclosure of which is incorporated by reference in its entirety.
The present invention relates to a novel polyorganosiloxane capable of producing a copolycarbonate having improved weather resistance and fluidity, and a copolycarbonate produced using the same.
Background
Polyorganosiloxane as a polysiloxane refers to a polymer having a siloxane bond substituted with an organic group as a main chain. For example, polyorganosiloxanes are prepared by condensation polymerization of aromatic diols such as bisphenol a with carbonate precursors such as phosgene, are colorless, odorless, resistant to oxidation, are hypoallergenic (hypoallergenic) insulators that are stable at room temperature, and are used in electrical, electronic, vehicular, mechanical, pharmaceutical, cosmetic, lubricant, adhesives, gaskets, artificial aids for orthopedic surgery, and the like.
In addition, polyorganosiloxanes have excellent impact strength, dimensional stability, heat resistance, transparency, and the like, and are applied in various fields such as exterior materials for electronic and electrical products, vehicle parts, building materials, optical elements, and the like. Recently, many studies have been made to apply copolycarbonate resins in more fields in which monomers having different structures are introduced into the main chain of polycarbonate by copolymerizing two or more aromatic diols having different structures to obtain desired properties.
In particular, studies have also been conducted to introduce a polysiloxane structure into the main chain of polycarbonate. However, most of the techniques have disadvantages of high production costs and of not being able to improve both chemical resistance and impact strength.
However, as the field of application of copolycarbonates expands, higher weather resistance and fluidity are required for the copolycarbonates, and therefore, a copolycarbonate of a novel structure capable of improving the weather resistance and fluidity while maintaining inherent physical properties thereof is required.
Disclosure of Invention
Technical problem
The present invention provides a novel polyorganosiloxane capable of producing a copolycarbonate having improved weather resistance and fluidity.
Further, the present invention provides a copolycarbonate prepared using the polyorganosiloxane.
Furthermore, the present invention provides a molded article manufactured using the copolycarbonate.
Technical scheme
The present invention provides a polyorganosiloxane represented by the following chemical formula 1.
Further, the present invention provides a copolycarbonate having a weight average molecular weight of 1,000g/mol to 100,000g/mol and comprising a repeating unit represented by the following chemical formula 2 and a repeating unit represented by the following chemical formula 3.
Furthermore, the present invention provides a molded article manufactured using the copolycarbonate.
Hereinafter, polyorganosiloxanes, copolycarbonates, and molded articles according to embodiments of the present invention will be described in more detail.
According to an embodiment of the present invention, there is provided a polyorganosiloxane represented by the following chemical formula 1:
[ chemical formula 1]
B-A-B
Wherein A is
B is
R1To R4Each independently is hydrogen or C1-10An alkyl group, a carboxyl group,
R5is hydrogen, halogen, hydroxy, C1-10Alkyl radical, C1-10Alkoxy or C6-10An aryl group, a heteroaryl group,
R6to R9Each independently is hydrogen, C1-10An alkyl group or a halogen, in which,
x is-CO-or-CO- (C)6-10Arylene) -CO-,
y is C1-10An alkylene group or a substituted alkylene group,
z is a bond, -OCO-or-COO-,
w is a radical containing- (C)1-10Alkylene) -O-divalent functional groups,
n is an integer of 1 to 99.
Polyorganosiloxane as a polysiloxane refers to a polymer having a siloxane bond substituted with an organic group as a main chain. Among the polyorganosiloxanes, in particular, the polyorganosiloxane of one embodiment represented by chemical formula 1 may exhibit both the effect due to the siloxane monomer and the effect due to the linker and the ester structure represented by a of chemical formula 1. Therefore, the polyorganosiloxane is characterized by having improved weather resistance due to fries rearrangement (frierarangement) effect, and improved fluidity due to improvement of internal chain mobility of ester structure and ether structure, while maintaining high ductility.
In addition, W in chemical formula 1 preferably contains- (C)1-10Alkylene) -COO- (C)1-10Alkylene) -O-.
Furthermore, A is more preferably
Further, in chemical formula 1, R1To R4Preferably each independently hydrogen or C1-4An alkyl group.
Furthermore, R5Preferably hydrogen or C1-4An alkoxy group.
Furthermore, R6To R9Preferably each independently hydrogen or C1-4An alkyl group.
Furthermore, X is preferably-CO- (phenylene) -CO-.
Furthermore, Y is preferably C1-5An alkylene group.
In addition, specific examples of the polyorganosiloxane represented by chemical formula 1 may be the following compounds:
wherein A is
Meanwhile, the polyorganosiloxane of one embodiment may be synthesized by the method in the following reaction scheme 1, but is not limited thereto, and the preparation method of the compound represented by chemical formula 1 will be described in more detail in the examples described below:
[ reaction scheme 1]
Wherein R is1To R5X, Y, Z and n are the same as defined in chemical formula 1, R14Is hydroxy or halogen, preferably hydroxy or chloro.
Step 1 is a step of preparing a compound represented by chemical formula 1-4 by reacting a compound represented by chemical formula 1-2 with a compound represented by chemical formula 1-3 as a carbonate-based compound. In this regard, the molar ratio of the compound represented by chemical formula 1-2 to the compound represented by chemical formula 1-3 is preferably 1:1.1 to 1:5, more preferably 1:1.3 to 1:2.5, and in the reaction, chloroform is preferably used as a solvent. Furthermore, the reaction is preferably carried out at room temperature.
According to another embodiment of the present invention, there is provided a copolycarbonate having a weight average molecular weight of 1,000g/mol to 100,000g/mol and including a repeating unit represented by the following chemical formula 2 and a repeating unit represented by the following chemical formula 3:
[ chemical formula 2]
Wherein A is
R1To R4Each independently is hydrogen or C1-10An alkyl group, a carboxyl group,
R5is hydrogen, halogen, hydroxy, C1-10Alkyl radical, C1-10Alkoxy or C6-10An aryl group, a heteroaryl group,
R6to R9Each independently is hydrogen, C1-10An alkyl group or a halogen, in which,
x is-CO-or-CO- (C)6-10Arylene) -CO-,
y is C1-10An alkylene group or a substituted alkylene group,
z is a bond, -OCO-or-COO-,
w is a radical containing- (C)1-10Alkylene) -O-divalent functional groups,
n is an integer of 1 to 99,
[ chemical formula 3]
Wherein, X1Is unsubstituted or substituted by phenyl1-10Alkylene radical, C3-6Cycloalkylene, O, S, SO2Or a combination of CO and at least one of CO,
R10to R13Each independently is hydrogen, C1-10Alkyl or halogen.
In chemical formula 2, A, R1To R9X, Y, Z and n are the same as described in chemical formula 1 without limitation.
X1Preferably unsubstitutedOr C substituted by phenyl1-4Alkylene radical, C3-6Cycloalkylene, O, S, SO2Or CO.
Furthermore, R10To R13Preferably each independently hydrogen, C1-4Alkyl, chlorine or bromine.
The copolycarbonate according to an embodiment may be prepared by polymerizing a polyorganosiloxane represented by chemical formula 1, an aromatic diol compound, and a carbonate precursor, and as described above, the copolycarbonate is characterized by having improved weather resistance and flowability while maintaining ductility of the copolycarbonate due to improvement of internal mobility caused by an ester or ether structure in the polyorganosiloxane represented by chemical formula 1.
The aromatic diol compound is a compound represented by the following chemical formula 4, and corresponds to chemical formula 3:
[ chemical formula 4]
Wherein, X1And R10To R13The same as defined in chemical formula 3.
Specific examples of the aromatic diol compound may include: bis (4-hydroxyphenyl) methane, bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) sulfoxide, bis (4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) ketone, 1-bis (4-hydroxyphenyl) ethane, 2-bis (4-hydroxyphenyl) propane (bisphenol A), 2-bis (4-hydroxyphenyl) butane, 1-bis (4-hydroxyphenyl) cyclohexane (bisphenol Z), 2-bis (4-hydroxy-3, 5-dibromophenyl) propane, 2-bis (4-hydroxy-3, 5-dichlorophenyl) propane, 2-bis (4-hydroxy-3-bromophenyl) propane, 2-bis (4-hydroxy-3-chlorophenyl) propane, 2, 2-bis (4-hydroxy-3-methylphenyl) propane, 2-bis (4-hydroxy-3, 5-dimethylphenyl) propane or 1, 1-bis (4-hydroxyphenyl) -1-phenylethane.
The carbonate precursor is used to link the compound represented by chemical formula 1 with the compound represented by chemical formula 4, and specific examples thereof may include: phosgene, triphosgene, diphosgene, bromophosgene, dimethyl carbonate, diethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, diphenyl carbonate, ditolyl carbonate, bis (chlorophenyl) carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis (biphenyl) carbonate, or bishaloformate (bishaloform).
In addition, the copolycarbonate of one embodiment may be prepared by a method including the step of polymerizing a composition including the polyorganosiloxane represented by chemical formula 1, the aromatic diol compound, and the carbonate precursor.
The polyorganosiloxane represented by chemical formula 1 may be used in an amount of 0.1% by weight or more, 1% by weight or more, or 3% by weight or more, and 20% by weight or less, 10% by weight or less, or 7% by weight or less, based on 100% by weight of the composition, at the time of polymerization.
Further, the aromatic diol compound may be used in an amount of 40 wt% or more, 50 wt% or more, or 55 wt% or more, and 80 wt% or less, 70 wt% or less, or 65 wt% based on 100 wt% of the composition.
Further, the carbonate precursor may be used in an amount of 10 wt% or more, 20 wt% or more, or 30 wt% and 60 wt% or less, 50 wt% or less, or 40 wt% or less based on 100 wt% of the composition.
In this regard, the polymerization may preferably be carried out by interfacial polymerization. In the interfacial polymerization process, the polymerization reaction can be carried out at normal pressure and low temperature, and the molecular weight can be easily controlled.
The polymerization temperature is preferably 0 ℃ to 40 ℃ and the reaction time is preferably 10 minutes to 5 hours. Further, the pH is preferably maintained above 9 or above 11 during the reaction.
The solvent that can be used in the polymerization is not particularly limited as long as it is a solvent generally used in the art for polymerization of copolycarbonate, for example, halogenated hydrocarbon such as dichloromethane, chlorobenzene, and the like.
Further, the polymerization is preferably carried out in the presence of an acid binder, and the acid binder may be an alkali metal hydroxide such as sodium hydroxide, potassium hydroxide, or the like, or an amine compound such as pyridine, or the like.
In addition, in order to control the molecular weight of the copolycarbonate during polymerization, the polymerization is preferably carried out in the presence of a molecular weight modifier. As molecular weight regulator, C can be used1-20An alkylphenol. Specific examples thereof may include: p-tert-butylphenol, p-cumylphenol, decylphenol, dodecylphenol, tetradecylphenol, hexadecylphenol, octadecylphenol, eicosylphenol, docosylphenol or triacontylphenol. The molecular weight regulator may be added before, during or after initiation of polymerization. The content of the molecular weight regulator may be, for example, 0.01 parts by weight or more, 0.1 parts by weight or more, or 1 part by weight or more, and 10 parts by weight or less, 6 parts by weight or less, or 5 parts by weight or less, based on 100 parts by weight of the aromatic diol compound. Within the range, a desired molecular weight can be obtained.
In order to accelerate the polymerization reaction, a reaction accelerator may also be used, for example, tertiary amine compounds such as triethylamine, tetra-n-butylammonium bromide, tetra-n-butylphosphonium bromide, etc., quaternary ammonium compounds, quaternary phosphonium compounds.
In addition, the present invention provides a molded article manufactured using the copolycarbonate. As described above, due to the structure derived from polypropylene glycol in the polyorganosiloxane represented by chemical formula 1, fluidity is improved while ductility of copolycarbonate is maintained, and thus the molded article can be applied to various fields as compared to molded articles manufactured using previous copolycarbonates.
In addition to the copolycarbonate according to the invention, the molded article may further contain one or more selected from the group consisting of an antioxidant, a plasticizer, an antistatic agent, a nucleating agent, a flame retardant, a lubricant, an impact modifier, a fluorescent brightener, an ultraviolet absorber, a pigment, and a dye, as necessary.
The method of manufacturing the molded article may include, for example, the steps of: the copolycarbonate of the present invention and other additives are mixed by a mixer, the mixture is extrusion-molded by an extruder to prepare pellets, the pellets are dried, and then the dried pellets are injected by an injection molding machine.
Advantageous effects
The novel polyorganosiloxanes according to the present invention can be used as monomers for copolycarbonates and can have improved weather resistance and flowability while maintaining inherent physical properties such as ductility of the copolycarbonates.
Detailed Description
The present invention will be described in more detail with reference to the following examples. However, the following examples are for illustrative purposes only, and the disclosure of the present invention is not intended to be limited by the following examples.
Example 1:
(step 1) preparation of polyorganosiloxane
To a 2,000m L three-necked reflux flask was added 1,000m L (liquid) of chloroform (CHCl)3) 11.7g of Antioxidant-245 (ethylenebis (oxyethylene) bis [3- (5-tert-butyl-4-hydroxy-m-tolyl) propionate was slowly dissolved at room temperature over 1 hour under a nitrogen atmosphere]Mw: 586g/mol) and 7.1g of terephthaloyl chloride. Then, 25g of triethylamine was added and allowed to react for 1 hour, and 210g of allylphenol polydimethylsiloxane (n: 43, Mw: 3,500g/mol) was added and sufficiently reacted to prepare a compound represented by the above formula1The H NMR chart is shown in FIG. 1.
(step 2) preparation of copolycarbonate resin
232g of bisphenol A, 1,784g of distilled water and 385g of sodium hydroxide were added to the polymerization reactor and mixed under a nitrogen atmosphere to completely dissolve the bisphenol A. Then 875g of methylene chloride, 4.3g of PTBP (p-tert-butylphenol), and 7.0g (5.2 wt% based on solids of polycarbonate resin) of the compound prepared in step 1 were added and mixed. To this was added dropwise 130g of TPG (triphosgene) dissolved in 920g of dichloromethane over 1 hour, at which time the pH was kept at 11 using an aqueous sodium hydroxide solution. After the dropwise addition was completed, the solution was aged for 15 minutes, andmethylene chloride in which 46g of triethylamine was dissolved was added thereto. After a total reaction time of 1 hour and 30 minutes, the pH was lowered to 4 and three washes with distilled water were performed to separate the dichloromethane phase. The polymer thus obtained was precipitated in methanol and dried at 120 ℃ to obtain a final powdery copolycarbonate resin. It is composed of1The H NMR is graphically represented in fig. 2.
Example 2
A copolycarbonate resin was prepared in the same manner as in example 1, except that 120g of allylphenol polydimethylsiloxane (n: 22, Mw: 2,000g/mol) was used in place of the allylphenol polydimethylsiloxane (n: 43, Mw: 3,500 g/mol).
Example 3
A copolycarbonate resin was prepared in the same manner as in example 1, except that 3.5g (2.6 wt% of the polycarbonate resin based on the solid) of the compound prepared in step 1 was used in step 2 instead of 7.0 g.
Comparative example 1
A copolycarbonate resin was prepared in the same manner as in example 1, except that the compound prepared in step 1 was not used in step 2.
Test example: evaluation of physical Properties of copolycarbonate resin
The copolycarbonate resins obtained in examples 1 to 3 and comparative example 1 were pelletized to prepare samples for evaluation of physical properties, and the physical properties of the samples were measured by the following methods. The results are shown in table 1 below.
(1) Flow (MFR, g/10 min): the samples were used for the determination according to the standard ASTM D1238 (at 300 ℃ and 1.2 kg).
(2) Room-temperature impact strength and low-temperature impact strength (notched Izod, J/m): measured according to ASTM D256(1/8 inches, notched Izod) at 23 ℃ and-30 ℃ respectively.
(3) Weather resistance (△ YI, 500 hours) the difference in yellowness index (△ YI) of the samples was measured according to ASTM D4329 over 500 hours using a QUV-A accelerated weathering tester (Q-L AB).
(4) Weight average molecular weight (Mw, g/mol): the measurement was carried out by weighing with PC standards using Agilent 12000 series GPC.
[ Table 1]
As shown in Table 1, it can be found that the copolycarbonate resins prepared in examples have the same or higher flowability and room temperature impact strength as compared with comparative example 1, while having very excellent low temperature impact strength at-30 ℃ and weather resistance.
The copolycarbonate resins of the examples have excellent low-temperature impact strength and weather resistance maintaining inherent physical properties of polycarbonate resins when subjected to various weather, and thus are easily applied to various fields such as exterior materials for electronic and electrical products, vehicle parts, and building materials.
Claims (12)
1. A polyorganosiloxane represented by the following chemical formula 1:
[ chemical formula 1]
B-A-B
Wherein A is
B is
R1To R4Each independently is hydrogen or C1-10An alkyl group, a carboxyl group,
R5is hydrogen, halogen, hydroxy, C1-10Alkyl radical, C1-10Alkoxy or C6-10An aryl group, a heteroaryl group,
R6to R9Each independently is hydrogen, C1-10An alkyl group or a halogen, in which,
x is-CO-or-CO- (C)6-10Arylene) -CO-,
y is C1-10An alkylene group or a substituted alkylene group,
z is a bond, -OCO-or-COO-,
w is a radical containing- (C)1-10Alkylene) -O-divalent functional groups,
n is an integer of 1 to 99.
2. The polyorganosiloxane according to claim 1, wherein W is a group comprising- (C)1-10Alkylene) -COO- (C)1-10Alkylene) -O-.
3. The polyorganosiloxane according to claim 1, wherein A is
4. The polyorganosiloxane according to claim 1, wherein R1To R4Each independently is hydrogen or C1-4An alkyl group.
5. The polyorganosiloxane according to claim 1, wherein R5Is hydrogen or C1-4An alkoxy group.
6. The polyorganosiloxane according to claim 1, wherein X is-CO- (phenylene) -CO-.
7. The polyorganosiloxane according to claim 1, wherein Y is C1-5An alkylene group.
8. The polyorganosiloxane according to claim 1, wherein the polyorganosiloxane has the following structure:
wherein A is
9. A copolycarbonate having a weight average molecular weight of 1,000g/mol to 100,000g/mol and comprising a repeating unit represented by the following chemical formula 2 and a repeating unit represented by the following chemical formula 3:
[ chemical formula 2]
Wherein A is
R1To R4Each independently is hydrogen or C1-10An alkyl group, a carboxyl group,
R5is hydrogen, halogen, hydroxy, C1-10Alkyl radical, C1-10Alkoxy or C6-10An aryl group, a heteroaryl group,
R6to R9Each independently is hydrogen, C1-10An alkyl group or a halogen, in which,
x is-CO-or-CO- (C)6-10Arylene) -CO-,
y is C1-10An alkylene group or a substituted alkylene group,
z is a bond, -OCO-or-COO-,
w is a radical containing- (C)1-10Alkylene) -O-divalent functional groups,
n is an integer of 1 to 99,
[ chemical formula 3]
Wherein, X1Is unsubstituted or substituted by phenyl1-10Alkylene radical, C3-6Cycloalkylene, O, S, SO2Or a combination of CO and at least one of CO,
R10to R13Each independently is hydrogen, C1-10Alkyl or halogen.
10. The copolycarbonate of claim 9, wherein X1Is unsubstituted or substituted by phenyl1-4Alkylene radical, C3-6Cycloalkylene, O, S, SO2Or CO.
11. The copolycarbonate of claim 9, wherein R10To R13Each independently is hydrogen, C1-4Alkyl, chlorine or bromine.
12. A molded article produced using the copolycarbonate according to any one of claims 9 to 11.
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| KR10-2015-0125677 | 2015-09-04 | ||
| KR1020150125677A KR101948823B1 (en) | 2015-09-04 | 2015-09-04 | Novel polyorganosiloxane, and copolycarbonate prepared by using the same |
| PCT/KR2016/009044 WO2017039190A1 (en) | 2015-09-04 | 2016-08-17 | Novel polyorganosiloxane and copolycarbonate prepared using same |
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| KR20160002485A (en) | 2014-06-30 | 2016-01-08 | 주식회사 삼양사 | Polysiloxane-polycarbonate copolymer having improved transparency and low temperature impact resistance and method for preparing the same |
| KR101687683B1 (en) * | 2014-09-05 | 2016-12-19 | 주식회사 엘지화학 | Copolycarbonate and composition comprising the same |
| KR20160067714A (en) * | 2014-12-04 | 2016-06-14 | 주식회사 엘지화학 | Copolycarbonate and article containing the same |
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- 2016-08-17 JP JP2018502375A patent/JP6498840B2/en active Active
- 2016-08-17 US US15/742,000 patent/US10577461B2/en active Active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102822241A (en) * | 2010-03-29 | 2012-12-12 | 株式会社三养社 | Hydroxy-terminated siloxane, polysiloxane-polycarbonate copolymer, and preparation method thereof |
| CN103958573A (en) * | 2011-10-31 | 2014-07-30 | 株式会社三养社 | Polysiloxane-polycarbonate copolymer and method of manufacturing the same |
| CN104066773A (en) * | 2012-01-20 | 2014-09-24 | 沙特基础创新塑料Ip私人有限责任公司 | Articles prepared from thermoplastic compositions, and method of preparing such articles |
Also Published As
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| JP6498840B2 (en) | 2019-04-10 |
| TWI709588B (en) | 2020-11-11 |
| KR20170028704A (en) | 2017-03-14 |
| PL3301123T3 (en) | 2019-09-30 |
| TW201718701A (en) | 2017-06-01 |
| CN107849254A (en) | 2018-03-27 |
| JP2018525477A (en) | 2018-09-06 |
| EP3301123B1 (en) | 2019-04-10 |
| KR101948823B1 (en) | 2019-02-15 |
| US20180194894A1 (en) | 2018-07-12 |
| EP3301123A1 (en) | 2018-04-04 |
| US10577461B2 (en) | 2020-03-03 |
| WO2017039190A1 (en) | 2017-03-09 |
| EP3301123A4 (en) | 2018-07-04 |
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